Flavor compositions and processes

ABSTRACT

Enhancement of the flavor of foodstuffs is achieved by the addition of a small but effective amount of 2-nonenal, and/or 2nonenol. Particular derivatives of both the alcohol and the aldehyde are also useful.

United States Patent 1191 Parliment et al.

[4 1 May 27, 1975 1 FLAVOR COMPOSITIONS AND PROCESSES [75] Inventors:Thomas H. Parliment, Valley Cottage; William P. Clinton, Monsey, both ofN.Y.; Richard Scarpellino, Ramsey, N.J.; Robert J. Soukup, New City;Martin F. Epstein, Pearl River, both of NY.

[73] Assignee: General Foods Corporation, White Plains, NY.

221 Filed: Apr. 11, 1972 211 Appl. No.: 243,055

52 us. c1. 426/573; 426/577; 426/576; 6 426/593; 426/590; 426/599;426/598; 426/641; 426/660 51 Int. Cl A231 1/26 [58] Field of Search99/140 R; 426/175, 350

[56] References Cited UNITED STATES PATENTS 3,655,397 4/1972 Parlimentet a1 99/140 R OTHER PUBLICATIONS Chemical Abstracts, 70:2553b (1969).Chemical Abstracts, 73:32290t (1970). Chemical Abstracts, 74:98137a(1971).

Primary ExaminerMorris O. Wolk Assistant Examiner-Sidney MarantzAttorney, Agent, or Firm-Bruno P. Struzzi; Thomas R. Savoie; Daniel J.Donovan [5 7] ABSTRACT Enhancement of the flavor of foodstuffs isachieved by the addition of a small but effective amount of 2- nonenal,and/or 2-nonenol. Particular derivatives of both the alcohol and thealdehyde are also useful.

19 Claims, No Drawings FLAVOR COMPOSITIONS AND PROCESSES Thisapplication is a continuation-in-part of application Ser. No. 129,609,filed Mar. 30, 1971, now US. Pat. No. 3,655,397 issued Apr. 11, 1972which is a continuation-in-part of application Ser. No. 867,887, filedOct. 20, 1969 for Flavor Compositions and Processes, now abandoned andapplication Ser. No. 857,227, filed Sept. 1 l, 1969, for Flavorcompositions and Processes,

now abandoned.

BACKGROUND OF THE INVENTION 1. Field of the Invention The presentinvention relates to 2-nonena1, and 2- nonenol, woody flavor compoundsfound to be useful in the area of flavor note alteration whether by theenhancement of flavor or flavor notes that are characteristic in asubstance, by modification of a flavor or flavor note from a less to amore desirable one, or by the complete or partial masking of a flavor orflavor note. Still more particularly, the invention relates toincorporation of the above-mentioned compounds and mixtures thereof infood to reduce the caramel, acid and sour flavor of food, and modify andimprove the green, earthy and buttery notes of coffee, and add adesirable woody, flavor note to foodstuffs.

2. Description of the Prior Art In the field of flavor enhancement, ithas been general practice to employ synthetic and naturally isolatedcompounds and compositions to enhance and/or mask the flavor offoodstuffs. The enhancement of flavor is extremely complex, eachindividual flavor containing literally hundreds of compounds, each ofwhich produces, to some degree, a flavor impact. In general, theisolation of a single flavor does not allow one to predict equivalentflavors, since compounds of greatly differing structure have been foundto produce approximately the same flavor character, while compounds ofsimilar structure frequently differ appreciably in taste. Consequently,the identification of desirable flavor components requires synthesis andtrial of individual candidates until compounds are identified which havedesirable flavor notes.

In the area of flavor enhancement of coffee flavored foodstuffs,especially soluble spray dried and freeze dried coffee and regularcoffee, thousands of compounds have been screened over the years in anattempt to isolate desirable components of coffee flavor. For manyyears, coffee technologists have searched for a flavor enhancingcompound which would produce the flavor note generally described byexperts as woody.

Trans-2-nonenal and trans-2-nonenol are old compounds, but theirpresence in coffee has not apparently been reported.

Trans-2-nonenal is formed from the oxidative fission of thehydroperoxide of methyl oleate and is found in the essential oil ofAchasma walang Val and in cranberries, cucumbers and carrots. 2-nonenalis suggested as a GRAS substance among many others in Food Technology,Vol. 24, pp 533-41, May 1970.

Synthesis of trans-2-nonenol, trans-2-nonenal and its acetals have beenreported in the literature.

Organoleptically, we suspected that either trans-2- nonenal ortrans-2-nonenol were present in certain fractions of coffee, such aspercolated, roasted and ground brew, roasted coffee oil, and steamgenerated roasted and ground coffee aroma. The similarity of the woodyflavor of these coffee fractions and trans-2- nonenal andtrans-2-nonenol is apparent to expert tasters.

We have recently found trans-Z-nonenal to be present in Columbian greenand roasted coffee as well as aroma fractions of roasted coffee.

The presence of woody compounds, which are the subject of thisinvention, in soluble coffee, especially spray dried soluble, isunlikely since flavor experts organoleptically do not detect a woodyflavor or aroma in these coffees.

Trans-2-nonenal is characterized by flavor experts to have anunpleasant, rancid fat flavor when tasted at conventional flavorconcentrations of 50 ppm or higher. Trans-2-nonenol has similar fattycharacterisitcs as does cis-2-nonenol. The acetals and esters have afatty flavor but at much higher levels exceeding one part per million.Aroma quality is judged as pungent and unpleasant at the fatty flavorconcentrations.

SUMMARY OF THE INVENTION The general purpose of this invention is toprovide 2-nonenol and 2-nonenal compounds and compositions which willenhance the flavor of foodstuffs.

The flavor enhancement is achieved by the addition of a small buteffective amount of 2-nonenal, 2- nonenol, lower alkyl acetals of2-nonenal, esters of organic acid anhydrides and 2-nonenol in which thecarbonyl group is not conjugated with a double bond or aromatic ring andmixtures thereof to the food to be flavored.

The 2-nonenal, 2-nonenol and mixtures thereof produce a coffee flavorwhen added in minute amounts (well below 25 ppm and generally in therange of 0.05 to 16 ppb) to water or foodstuffs. The acetal derivativesgive a similar woody flavor at the previously mentioned concentrationsbut do not exhibit fatty undesirable flavor until levels of one part permillion (ppm) are approached. The ester derivatives have a higherthreshold flavor level of about 50-100 ppb with fatty flavor apparent inthe parts per million concentration. In one respect, the derivatives areadvantageous as flavoring agents since a wider range of woody flavorconcentrations are possible. The woody flavor compounds of thisinvention mask typically undesirable flavors, balance overall flavor andimpart a regular coffee flavor generally described by experts as woody.

The ability of the woody flavor compounds to produce a woody flavor andto balance and/or hide undesirable flavors is unexpected. Thesecompounds, when incorporated at conventional flavor levels infoodstuffs, produce a flavor characterized by experts as an unpleasantcucumber, green fatty to rancid fat flavor totally unsuitable forcoffee. Only at extremely low concentration is the woody flavor apparentand useful.

Foodstuffs including beverages which can be flavored with the flavoringagent of this invention include, for instance, ice cream; confectionerygoods such as boiled sweets, hard candy, fillings, fondants, jellies andthe like; meat products; custards; yogurt; milk drinks; syrups;carbonated beverages; spirits; liqueurs gelled deserts including gelatindeserts, cereal based beverages and the like.

The woody flavored compounds of this invention, and mixtures thereof,can be employed to contribute a slightly woody flavor to foods such ascola, ginger ale and other beverages, both carbonated and noncarbonated.They are employed at concentrations below the flavor threshold to maskor hide undesirable flavors or to enhance flavors desirable in the foodtreated.

It is an object of this invention to provide a flavoring agent which iscapable of imparting a woody flavor and aroma to foodstuffs includingbeverages.

A further object of this invention is to provide an enhancing agentwhich can be added to naturally or synthetically flavored foodstuffs inorder to improve or enhance the flavoring properties thereof and makemore natural their flavor and aroma.

Another object of this invention is to provide foodstuff having enhancedflavor and aroma.

Still another object of this invention is to provide a method forenhancing the flavor of foodstuffs. of foodstuffs.

DESCRIPTION OF THE INVENTION The compounds employed in the compositionsand processes of this invention are:

trans-Z-nonenal I ll CH3 (CH2) c c c H trans-Z-nonenol CH (CH C CH oHcis-2-nonenol CH (CH 5 C C CH OH cis-Z-nonenal H H O I I ll c11 (CH 5 cc c H acetals of 2-nonenal l CH (CH c1: c1: c 3 2 5 oR Where R is loweralkyl.

esters of organic acids and 2-nonenol in which the carbonyl is notconjugated with a double bond or aromatic ring.

Where R, is hydrogen or lower alkyl or substituted lower alkyl.

Trans-2-nonenal and the trans-2-nonenal acetals are obtained by theprocess described by Paul Z. Bedoukian, Preparation of a, B-UnsaturatedAldehyde Dimethyl Acetals and Their Free Aldehydes, J.A.C.S., 79, 889-92(1957).

The saturated aldehyde is converted to the enol acetate and thenbrominated in carbon tetrachloride. On adding methanol to the brominatedmixture, the dimethyl acetal of a-bromo-aldehyde is obtained. Ontreatment of the latter with potassium hydroxide in butanol there isobtained the unsaturated acetal which is converted to the a,B-unsaturated aldehyde by acid hydrolysis. If desired, the aldehyde canbe reduced using lithium aluminum hydride to the corresponding (1, B-unsaturated alcohol.

Trans-2-nonenal is also prepared by the reduction of the imide chlorideof a-nonenoic acid, Ber., 67B, 269 (1934); the hydrolysis of1,1-dichloro-3-bromononane, J.O.C. 13,895 (1948), US. Pat. No.2,574,832; by the oxidation of the corresponding alcohol, Bull. soc.chim. 53, 301 (1933), J.A.C.S. 70,2601 (1948); and by the oxidation of9,10,12-trihydroxy stearic acid, J.A.C.S. 62, 2305 (1940).

Trans-2-nonenol is prepared via the Knovenagel condensation usingn-heptanal and monoethyl malonate to give ethyl 2-nonenoate. Reductionof this ester with LiAll-L, followed by hydrolysis gives the unsaturateda1- cohol (J.A.C.S. 70, 2601 (1948)). If desired, the alcohol can beoxidized to trans-Z-nonenal by dichromate.

The acetals are prepared as per the method given in Advanced OrganicChemistry, R. C. Fuson, p. 368, John Wiley & Sons, (1950). Theunsaturated aldehyde is treated with an alcohol in the presence of anacidic catalyst such as ammonium chloride, boron trifluoride etherate,p-toluenesulfonic acid or the like. Cyclic acetals or dioxolanes areformed by 1,2-glycols such as ethylene glycol which react with theunsaturated aldehyde to yield the dioxolane. The a,B-unsaturatedaldehyde dimethyl acetals are prepared according to the procedure of P.Bedoukian, J.A.C.S., 79, 889-92 (1957).

The cis-2-nonenol is prepared by hydrogenation of commercially available2-nonyn-l-ol using a Lindlar type catalyst as per D. Cram and N.Allinger, J.A.C.S., 78, 2518 (1956).

The cis-2-nonenal is prepared according to the procedure of Thomas andWarburton, J.C.S., p. 2988 (1965).

The esters of organic acid anhydrides and 2-nonenol are prepared byreaction of the alcohol with anhydride in pyridine following theprocedure given in Wayner and Zook, p. 483, Synthetic Organic Chemistry,John Wiley & Sons (1953).

The following synthetic procedures are applicable to the synthesis ofsome of the preceeding compounds: Helv. Chim. Acta. 39, 1299 (1956);Compt. Rend. 247, 1627 (1958); Helv. Chim. Acta. 41, 1603 (1958); Gass.Chim. Ital. 88, 296 (1958); Chem & Ind. 202 (1960); and J.C.S. 1266(1961 2-nonenal, 2-nonenol, 2-nonenal dialkyl acetals and esters oforganic acid and 2-nonenol in which the carbonyl is not conjugated witha double bond or aromatic ring are employed as woody flavoringcompounds. The transform of the compounds are preferred woody flavoringagents particularly the alcohol and acetals. The woody flavor compoundsare useful for enhancing the flavor of food.

Nonenal, nonenol and derivatives of this invention are useful forenhancing the flavor of food, either by producing a woody flavor, or byreducing undesirable flavors in various products or by increasingdesirable flavors.

For example, when added to whisky, such as scotch, the woody compoundscontribute an excellent flavor. When added to carbonated andnon-carbonated beverages, trans-2-nonenal and trans-Z-nonenol produce alow level woody note not detectable as coffee flavor which enhances thebasic flavor of the beverage. Cola beverages are more like Coke, a woodycharacter in root beer improves it appreciably, etc.

In many foodstuffs the addition of the woody compounds of this inventionto the food reduces undesirable notes. For example, in cranberry juiceor jelly the compounds reduce astringency, and in synthetic flavoreddesserts and candies eliminate the cheap, candy character and produce asmoother, improved, more natural flavor. In sweet products such as mapleflavored syrup, they enhance the flavor and make the product smoother intaste.

In many foods the woody compounds increase desirable flavors. Forexample, beverages, as noted previously, exhibit a smoother and morenatural flavor. This is also true for puddings and other confectionssuch as ice cream, sherbert, candy and the like. In meat products, suchas fresh meat, broth, soups, hamburger and the like, the compoundsproduce a higher flavor impact and give the product a more meatycharacter.

The woody compounds are particularly useful for enhancing the flavor ofcereal based beverages prepared from roasted cereals such as wheat, rye,barley and the like which have been processed to form a solubilizedproduct. One such product, marketed under the trademark Postum eitherregular or coffee flavored is a dried water extract of roasted wheat,barley and molasses (see US3,021,218). The woody compounds reduce themolasses (caramel) flavor, characteristic of Postum and at proportionsabove threshold level additionally contribute a woody coffee likeflavor. They enhance coffee flavored foodstuffs, where a regular coffeenote characterized by coffee experts as woody is desired but deficient,such as some regular coffee like Robustas, decaffeinated coffee, solublecoffee, coffee flavored icing, coffee flavored carbonated andnoncarbonated soft drinks, coffee flavored beverages produced fromnon-coffee raw materials such as Postum brand beverage, coffee flavoreddesserts such as gelatin, ice cream, pudding, cakes, cookies and thelike, coffee flavored candies and the like, and other foodstuffs whichhave in part a coffee flavor such as mocha flavored foodstuffs. Inaddition, these compounds can be employed in foodstuffs normally usedwith coffee, such as coffee creamers, sweeteners, and the like, toimpart a coffee flavor.

The woody compounds employed in this invention and mixtures thereof givea coffee flavor when added to water or foodstuffs in minute amounts. Inaddition to imparting a coffee like flavor having a strong woody note,these compounds exert a balancing effect on other desirable coffee notessuch as the green, earthy and buttery notes, while masking theundesirable acid, sour and caramel notes.

In spray dried soluble coffee, the woody compounds and mixtures thereofenhance the woody character of the brew, while masking the caramelflavor. In addition, they exert a desirable blending effect on theoverall brew flavor.

In freeze dried soluble coffee, the woody compounds and mixtures thereofcontribute a woody note, and blend the winey, buttery notes, giving amore balanced flavor while hiding sourness.

Similar effects are noted when the preceding compounds are added toprelightened soluble coffee, or when incorporated with roasted andground regular coffee.

When incorporated with foodstuffs containing other added coffee flavorfractions, both synthetic and those obtained from coffee, the woodycompounds and mixtures thereof enhance coffee flavor by balancing theother flavors and by strengthening the woody regular coffee flavor whichis deficient.

Depending on the flavor desired, the woody compounds or mixtures thereofcan be incorporated in the foodstuff either alone or combined with otherflavor ingredients and/or carriers.

It is particularly preferred to add a small but effective amount of the2-nonenal and 2-nonenol woody flavored compounds to soluble coffee whichis deficient either partially or totally in woody flavor to enhance theoverall flavor. Addition may be either to the regular coffee prior toextraction, the extract prior to drying, or may be plated on or mixedwith the dry coffee. Since only a minute amount of the flavor and aromacompounds is needed, it is preferred to incorporate them in an ediblecarrier or concentrate.

Because of the extremely low levelof the unsaturated woody compoundsnecessary for enhancing food, it is preferred to form a concentratewhich may then be incorporated in the foodstuff. The concentrate may bea liquid, syrup or solid, depending on its ultimate use.

The unsaturated alcohol or aldehyde and their woody derivatives may beincorporated in ethanol, propylene glycol, oils such as cottonseed,coffee, peanut or the like, or other edible vehicles to form aconcentrate for convenient shipping, storage and addition to thefoodstuffs. For example, oileither coffee or other vegetableoil-containing the woody flavor compounds or mixtures thereof may beplated on soluble coffee to enhance its flavor, or alternatively the oilcontaining the flavor compound may be incorporated in extract and driedto form an enhanced soluble coffee.

Dry concentrates containing the woody compounds and mixtures thereof mayalso be prepared employing film forming compositions such as gums likegum arabic, pectins, alginates and the like, starch breakdown productssuch as Capsul (National Starch), Morex I918 (Corn Products), Maltrin 10(Grain Processing) and the like, candy melt systems and other artrecognized stabilizing or diluent systems.

In forming any concentrate, the proportion of woody flavor compound ormixtures thereof in the concentrate is not critical, provided the levelof flavoring is controlled to provide for even distribution of theflavor concentrate throughout the foodstuff to be flavored.

Minute amounts of the woody flavor Z-nonenal and 2-nonenol compounds ormixtures thereof are sufficient to produce an enhancement of coffeeflavor in foodstuffs. For example, in a regular or soluble coffeebeverage, say from about I to 1.5 percent coffee solids brew, thefollowing flavor and aroma characteristics, defined by expert tasters,have been noted:

Undesired Fatty Flavor Threshold Recognition Becoming Flavoring LevelLevel Apparent pp p ppb cls-2-nonenol 3 0.5 34 trans-Z-nonenal 0.05-0.20.4-0.6 16 trans-2-nonenol 0,10-02 0.6 16 trans-2-nonene 0.03 0.08 800dimethyl Acetal trans-2-nonene diethyl acetal 0.02 0.03 1200 l-Octenyll-dioxolane 0.3 0.8 1000 trans-2-nonenylacetate 100 200 1500cis-2-nonenyl acetate 50 150 1500 The threshold level is that quantityof flavoring producing a change in cup flavor and aroma, but a changewhich cannot be described as a particular flavor. The recognition levelis the quantity of flavoring which can be defined as imparting a woodynote to the brew. The fatty level is that point where the undesirablefatty flavor becomes apparent and detracts from the woody character ofthe flavoring noted at lower levels. For coffee brew from 0.01 and morepreferably from 0.05 parts per billion (ppb) of the woody flavorcompounds and mixtures thereof are employed. Generally, there isemployed in the brew from 0.05 ppb to 16 ppb, with 0.1 ppb to ppbpreferred. A very desirable concentration for most of the 2-nonenal and2-nonenol woody flavored compounds which exert a balancing of desirableregular coffee flavor, imparts woodiness and masks undesirable carameland acid flavors is from 0.4 to 2.0 ppb. For the woody esters, higherconcentrations are necessary.

On a dry coffee solids basis, the following concentrations areequivalent to the brew concentrations previously noted:

The preferred concentration, particularly for dry soluble coffee, is 7.5to 380 ppb, and more preferably from 30 to 150 ppb on a dry coffeesolids basis.

The transform of the 2-nonenal and 2-nonenol and their derivatives arepreferred because of isomeration, with time, of the cisform. Of thetranscompounds the alcohol and acetal compounds are preferred over thealdehyde. The ester while stable requires higher concentrations todevelop a woody flavor and is less preferred to the alcohol.

The flavor impact of the woody compounds and mixtures thereof is easilyadjusted by varying the concentration of the flavoring compoundsemployed in the foodstuff. It is to be expected that adjustment will benecessary depending on the particular foodstuff being flavored. Initialpanel screening, by those of ordinary skill in the art, is used todetermine the threshold and proper strength level for the particularfoodstuff in which the flavor is to be employed.

The 2-nonenal and 2-nonenol woody flavored compounds are particularlyuseful for balancing and blending the natural flavor of spray dried andfreeze dried soluble coffee, decaffeinated coffee both soluble andregular, and regular coffee of various blends, particularly those havinga high Robusta content. The flavor compounds are particularly preferredfor imparting a woody flavor to the preceding coffees deficient in thatflavor.

Again, even at levels below the woody threshold level, balancing offlavor is noted by expert tasters. These flavor compounds are alsoparticularly useful when combined with steam generated natural coffeearomas or enhancers where there is produced a blending or smoothing ofcoffee aroma and flavor and a masking of the undesirable sourness andcaramel characteristics often associated with coffee.

Similar flavor improvement is obtained by employing the woody compoundsor mixtures thereof with synthetic coffee flavor compounds or withmixtures of synthetic and natural coffee aromas and flavors.

The woody compounds or mixtures thereof may be combined with foodstuffsor with edible diluents or carriers by art recognized methods. Forexample, a standard solution of trans-2-nonenal may be prepared bysimply mixing the nonenal with alcohol, coffee oil or other diluents inwhich it is soluble. The woody flavor compounds thereof may also beincorporated in water by dissolution in a larger excess or byemulsification. They may also be incorporated in solid foodstuffs orcarriers by forming a solution of the solid, adding the flavoring anddrying by conventional techniques. Alternatively, a liquid dispersion oremulsion can be formed containing the flavoring and the foodstuff andthe dispersion or emulsion dried to form a solid which may be ground ifdesired. For partially insoluble solids which contain water solublesolids, such as regular coffee, the woody compound may be incorporatedin a liquid carrier, such as coffee or other vegetable oil, and sprayedor otherwise coated on the food as a film. Alternatively, the flavorcompounds can be incorporated in a solid carrier and the carrier dryblended with the food. The technique employed is not critical, so longas there is obtained a uniform mixture of the flavoring compound and thefoodstuff.

In addition to the application of the woody flavor compounds infoodstuffs, these flavoring agents may also be employed in ediblesubstances, such as pharmaceuticals, where a woody, regular coffee noteis desired.

The invention is now illustrated, but not limited by, the followingexamples:

EXAMPLE 1 A. A mixture of one mole of nonanal, 2.5 moles of aceticanhydride, and 15 g. of anhydrous potassium acetate is refluxed for onehour and cooled. Excess acid is removed by a 2X wash with water,followed by 5% sodium carbonate wash to give l-nonen-l-yl acetate as arelatively pure oil.

The oil is mixed with 200 ml of carbon tetrachloride and cooled in anice bath. Bromine, diluted with an equal volume of carbon tetrachloride,is added slowly with agitation while maintaining the temperature below10C. Bromine addition is stopped when the bromine is no longerdecolorized. To the brominated mixture, containing 1,2-dibromononen-1-ylacetate, is added 500 ml of methyl alcohol with shaking and cooling. Themixture is allowed to stand two days with occasional shaking and thendiluted with 1.5 liters of water. The separated oil is washed withsodium carbonate solution until free of acid and then fractionallydistilled in the presence of a small amount of sodium carbonate to yield2-bromo-nonanal dimethyl acetal.

The separated oil (one mole) is added to amixture of 500 ml of methanolcontaining 2 moles of potassium hydroxide and 500 ml of butanol. Themixture is gently heated in a Claisen flask and the methanol allowed todistill off. When butanol begins to distill, the distillation is stoppedand the contents transferred to a roundbottomed flask and refluxed in anoil bath. After refluxing for one hour, the mixture is washed with waterand the oil fractionally distilled through a column in the presence ofpotassium hydroxide to yield 2-nonenal dimethyl acetal.

B. Twenty to 30 ml of the recovered acetal is mixed with an equal volumeof 50% citric acid solution and boiled gently in a Claisen flask.Methanol is allowed to boil off until the distillate temperature reaches95F, at which point distillation is stopped. The flask contents are 2Xwater washed, followed by a 5% sodium carbonate solution. The resultingoil is vacuum distilled to yield relatively pure trans-2-nonenal.Further purification is obtained, if desired, by gas chromatography.

C. Trans-2-Nonenal (8 g., 0.056 mole), trimethylorthoformate (10.6 g.,0.1 mole), methyl alcohol (10ml.) and ammonium chloride (0.5 g.) areheated at reflux for 3 hours under nitrogen. The contents are cooled,filtered, diluted with water and extracted with ether. The ether layeris washed with 5% sodium barcarbonate followed by water and dried oversodium sulfate. Concentration and distillation gives trans-2-nonenedimethyl acetal, b.p. 5064C/0.5 mm., 5 g.

EXAMPLE ll Malonic acid (342 g, 3.3 mole) is dissolved in 555 ml of drypyridine (slightly exothermic). The mixture is cooled in ice water andn-heptaldehyde (342 g, 3.0 mole) is added with stirring. After theaddition is complete, the ice bath is removed and the mixture allowed tostand at room temperature for 60 hours, and then heated on a steam bathfor 8 hours. The reaction mixture is poured onto an equal volume ofwater. The organic layer is separated, washed with 900 ml 25% HCl, takenup in benzene, washed with water and dried. Distillation under vacuumgave trans-2-nonenoic acid, b.p. 123C/2 mm, 297 g, 64 percent yield.

A. Thionyl chloride (131 g, 1.1 mole) is added to trans-2-nonenoic acid(156 g, 1.0 mole). Reaction occurs immediately with the evolution of HCland S0 After the initial reaction subsides, the mixture is heated slowlyto 130C. The dark mixture is vacuum distilled to yield trans-2-nonenoylchloride, b.p. 90C/2 mm, 155 g, 91 percent yield.

Trans-2-nonenoyl chloride (170 g, 1 mole) is dissolved in 500 ml ofdiglyme and placed in a flask fitted with a mechanical stirrer, drippingfunnel, low temperature thermometer and nitrogen inlet and outlet. Theflask is flushed with nitrogen and cooled to -78C in a dry ice acetonebath. To the flask, lithium tri-tbutoxyaluminohydried (254 g, 1 mole) in1,000 ml of diglyme is added over a period of 7 hours. The cooling bathis removed and the contents of the flask are allowed to warm to roomtemperature. The contents are poured onto crushed ice and the oily layertaken up in ether. The ether solution is dried over sodium sulfate,concentrated and vacuum distilled to give trans-2- nonenal.

Trans-2-nonenal (7.0 g, 0.05 mole) is dissolved in 50 ml of ehter andadded to a solution of LiAlH, (0.54 g, 0.014 mole) in 50 ml of ether atsuch a rate to maintain gentle refluxing. When the addition is complete,the so lution is refluxed for 1 hour. Ethyl acetate (2 ml) is added todestroy excess LiAl1-1.,. The mixture is aciditied with 5M HCl. Theether layer is separated washed 2X with water, and dried over sodiumsulfate. The ether solution is concentrated and the residue vacuumdistilled to yield trans-2-nonenol.

B. A 500 ml flask with a reflux condenser, mechanical stirrer and adropping funnel, and protected from moisture with a drying tube ischarged with LiAlH, (6.1 g, 0.16 mole) and 200 ml ether. A solution oftrans-2- nonenoic acid (7.8 g, 0.05 mole) in 25 ml ether is added at arate to maintain refluxing. Refluxing is continued for one hour and themixture cooled. Excess reagent is destroyed by the addition of ethylacetate (5 ml) followed by acidification with 5M HCl. The organic layeris separated, washed with water, dried and distilled under vacuum togive trans-2-nonenol.

EXAMPLE III A. Sodium (5.8 g, 0.25 mole) is dissolved in liquid ammonia(500 ml) and 2-nonyne diethyl acetal (10.6 g, 0.05 mole) in ether (15ml) is added dropwise to the solution over a thirty-minute period. Theresulting mixture is stirred for two hours and then quenched with anammonium chloride (16 g, 0.3 mole) and water (l00 ml) solution. Etherml) is added and the organic layer separated and washed successivelywith 3% sulfuric acid solution, 5% sodium bicarbonate solution andwater. The washed ether solution is dried over anhydrous sodium sulfate,concentrated and distilled to give 10 g. of trans-2-nonene diethylacetal, b.p. 6970C/0.1 mm. The acetal is purified using gas liquidpartition chromatography on diethylene glycol succinate.

B. Trans-2-Nonene diethyl acetal (21.4 g., 0.1 mole) is added tomethanol (250 ml). A Lindlar type catalyst, 5% Pd/BaSO (0.6 g) andquinoline (0.4 g) are added and the mixture placed on a mechanicalshaker for 1 hour. The catalyst is filtered and the solvent distilled.The residue is distilled under vacuum yielding a mixture of the threeacetals of nonenal, namely the diethyl, dimethyl, and ethylmethylacetals. Separation by gas chromatography on a diethylene glycolsuccinate column gives trans-2-nonene ethyl methyl acetal.

EXAMPLE IV Trans-2-nonenal (14.2 g, 0.1 mole), trimethylorthoformate (20g, 0.13 mole), ethylene glycol (16 g, 0.25 mole) and ammonium chloride(0.5 g) are heated over a range of 90-125C. Heating is continued untildistillation of ethyl formate and ethanol stops (-20 ml). The mixture isdiluted with water and extracted with ether. The ether extract is washedwith 5% sodium bicarbonate, water, dried over anhydrous sodium sulfateand concentrated. The residue is purifed using gas liquid partitionchromatography on OV-l 7, C, to give transl -octenyl-2-dioxolane.

EXAMPLE V 2-Nonyn-l-ol (20 g, 0.4 mole) in 200 ml methyl alcohol ishydrogenated in a Parr bomb using a Lindlar catalyst (0.5 g Pd/BaSO andquinoline (0.5 g). The hydrogenation was monitored by gas liquidpartition chromatography on diethylene glycol succinate. Hydrogenationis stopped when the concentration of the acetylenic alcohol equals thatof the saturated alcohol. The hydrogenation mixture is filtered, dilutedwith water and extracted with ether. The ether extract is dried overanhydrous sodium sulfate, concentrated and distilled to yield 13 g ofcis-2-nonen-l-ol, b.p. 60-64C/0.5 mm.

EXAMPLE VI A.Cis-2-nonenol g, mole) is stirred with manganese dioxide(50 g, mole) in ether (250 ml) at room temperature for 1 hour. Themixture is filtered, ether removed, and the residue distilled to givecis-2- nonenal.

B.Cis2-nonenol (2.9 g, 0.03 mole), acetic anhydride (3.1 g, 0.045 mole)and pyridine (15 ml) is heated at reflux for 3 hours. The solution iscooled and diluted with water. The organic layer is separated and washedsuccessively with 3% sulfuric acid, and water. The solution is driedover sodium sulfate and distilled under vacuum to yield cis-2-nonenylacetate, b.p. 58-62C/0.1 mm.

EXAMPLE VII Isobutyric acid (22.0 g, 0.25 mole), trans-2-nonen-1- 01(44.3 g, 0.25 mole), xylene (100 ml) and p-toluenesulfonic acid areheated to 145C. The solution is reflux ed for 5 minutes and 4.5 ml wateris collected by distillation. The reaction mixture is cooled and firstwashed with water followed by 5% sodium carbonate.

The washed solution is dried over sodium sulfate and distilled to yield34.1 g of trans-Z-nonenyl isobutyrate, b.p. 8788C/0.5 mm. An analyticalsample is obtained for taste evaluation using gas chromatography.

EXAMPLE VIII To a flask equipped with a reflux condenser, mechanicalstirrer and dropping funnel is added trans-2- nonenol (14.2 g, 0.1mole), N N-dimethylaniline (12 g, 0.1 mole) and 20 ml ether. To thestirred mixture is added dropwise phenylacetyl chloride (15.5 g, 0.1mole) at a rate to maintain a vigorous reflux of ether. After theaddition, the mixture is warmed on a water bath for 2 hours and thenallowed to stand several hours. The ether layer is separated from theprecipitate and extracted with sulfuric acid. The ether layer is driedover anhydrous sodium sulfide and purified up to give trans-2-nonenylphenylacetate.

EXAMPLE IX A.Formic acid (142 g, 3 moles) and acetic anhydride (400 g, 4moles) are mixed and allowed to stand overnight. The mixture is thenheated to 50C and maintained for 1 hour at 50C. The resulting product isdistilled under vacuum to give acetyl formate, 395 g, b.p. 4650C/46 mm.

B.Acetyl formate (39.6 g, 0.45 mole) is added dropwise to a cooledmixture of sodium formate (6.8 g, 0.10 mole) and trans-Z-nonen-l-ol(47.3 g, 0.33 mole). When the addition is complete, the reaction mixturetemperature is maintained at 60C for 7 hours. The mixture is cooled anddiluted with water. The organic layer is separated and washed with 5%sodium bicarbonate, water and then dried over sodium sulfate.Trans-2-nonenyl formate, 419 g is obtained on distillation, b.p.605C/50-55 mm.

EXAMPLE X Pyridine ml) and trans-Z-nonen-l-ol (28.4 g, 0.2 mole) areheated to C and acetic anhydride (30.6 g, 0.3 mole) is added dropwise.The reaction mixture is maintained at 110-l15 for 2 hours and 125C for 3hours. The mixture is cooled and washed with water, 5% sulfuric acid,and finally water. The solution is dried over sodium sulfate. Trans-2-nonenyl acetate, 33.0 g is obtained by vacuum distillation, b.p.70-5C/5055 mm.

EXAMPLE XI A.A. taste comparison was made of instant Maxwell House brandcoffee beverage containing 1.35% coffee solids enhanced with 1 ppb and 2ppb trans-Z-nonenal. When compared to control, the 2 ppb enhanced samplehad an improved woody regular coffee flavor and lacked the typicalcaramel and acid notes of the control. The 1 ppb enhanced sample did notgive a detectable woody flavor, but did balance or blend the coffeeflavor and masked the caramel and acid flavor of the control.

B.Example XIA was repeated employing a broader range of flavorenhancement. Expert tasters made the following comments compared tocontrol:

Concentration of trans-2-nonenal in the brew Flavor Comments detectablesubtle flavor subtle recognition of woodiness definite recognition ofwoodiness woody and smoother woody and groundsy high woody impacttallowy flavor 0 burnt, fatty burnt, fatty and rancid C.Example XIB wasrepeated with the trans-2- nonenal replaced by trans-2-nonenol:

Concentration of trans-Z-nonenol The flavor impact of the other woodyflavor compounds employed in this invention is determined in the samemanner.

EXAMPLE XII Spray dried instant Maxwell House brand coffee containing asynthetic, winey, buttery flavor was compared to an identical samplecontaining an additional 2 ppb trans-2-nonenal. The comparison was madeby prepar ing a 1.35% coffee solids brew and then adding from a dilutestandard solution sufficient trans-2-nonenal to give 2 ppb concentrationin one of the two brews.

The sample treated with trans-2-nonenal was found to have a verydesirable balanced flavor, having prominent winey, buttery and woodyregular coffee notes. The trans-2-nonenal sample had a far betterbalanced flavor, the nonenal apparently blending the desirable flavorswhile masking undesirable flavors.

A similar flavor effect is obtained when trans-2- nonenal is replaced bytrans-2-nonenol, cis-2-nonenol or the acetal or ester derivativesdescribed herein.

EXAMPLE XIII A comparison similar to Example XI was made using freezedried Maxim brand soluble coffee. The cup enhanced with 2 ppbtrans-2-nonenal had an improved woody regular coffee note. In addition,the typically winey and buttery notes of the coffee were better balancedand the typical sourness of the brew was masked. At 1 ppb, whilewoodiness was not evident, there was an improved balanced cup flavor anda reduction in sourness.

When expert tasters compare either trans-2-nonenal or trans-2-nonenol atthe 1 ppb and 2 ppb level, similar improvement in winey and butterynotes is apparent as well as a definite woody flavor. Similar tasteeffects are noted for the other woody flavor compounds of thisinvention.

EXAMPLE XIV EXAMPLE XV A. A comparison similar to Example XI was made ofspray dried instant Maxwell House soluble coffee, having added to the1.35% coffee solids brew lppb each of 2-methoxy-3-isobutyl pyrazine andtrans-Z-nonenal. Compared to control, the enhanced brew had a morerounded flavor containing more regular coffee notes.

B. When the above comparison is repeated employing different levels ofthe flavor additives, the following results are obtained:

Flavor Concentration in the Brew Flavor Comments trans- 2-methoxy-3-iso-Z-nonenal butyl pyrazine p b pp l 0.5 woody, subtle earthly flavor,

slightly green -Continued Flavor Concentration in the Brew FlavorComments trans- 2-methoxy-3'iso- 2-nonenal butyl pyrazine 4.0 0.5 goodbalance, less astringent,

smooth and groundsy 3.0 1.5 earthy, woody 2.0 1.0 woody, subtle earthyflavor.

slightly green C. When trans-2-nonenal is replaced by trans-2- nonenol,similar flavor changes are obtained.

D. When 2-methoxy-3-isobutyl pyrazine is replaced y Flavor Concentrationin the Brew trans- 2-methoxy-3-iso- 2-nonenal butyl pyrazine FlavorComments pp pp 0.25 0.025 nice cup flavor with winey,

buttery notes and a slight woody flavor 0.25 0.175 earthy note is tooprominent,

masking the winey notes 0.5 1.0 too earthy and green EXAMPLE XVI A tenpercent ethanolic solution of trans-2-nonenal (Compagnie Parenton,Croton-on-Hudson, New York) was passed through a Perkin-Elmer model 900gas chromatography unit having a 6-foot by Vs inch column packed with10% diethylene glycol succinate polyester on /90 Anakrom ABS. The majorcomponent representing trans-2-nonenal was collected, diluted with waterand vigorously shaken to give a 40 ppm standard solution. This materialwas evaluated in water at 2 ppb and 20 ppb and found to give a regularcoffee flavor characterized by experts as woody or spent grounds.Similar results were obtained for tests in soluble coffee.

Expert tasters find undesirable flavors at about 16 ppm for bothtrans-Z-nonenal and trans-2-nonenol which are not apparent to lessskilled tasters.

EXAMPLE XVII An expert panel flavor evaluation was made of trans-2-nonenal, purified as in Example XVI, at a level of two parts perbillion in instant Maxwell House brand soluble coffee at a 1.35% coffeesolids concentration. The panel initially found a slight spent groundsflavor which improved the regular brewed character of the coffee. Thepanel noted a desirable blending or mixing of flavor and a secondaryaromatic flavor similar to that produced by the addition of steamgenerated aroma.

EXAMPLE XVIII A flavor comparison, similar to Example XI, was made usingspray dried Sanka brand decaffeinated soluble coffee having addedthereto 2 ppb of trans-2- nonenal. Compared to control, the flavorenhanced brew had an improved woody flavor and good balance of cupflavor and aroma.

When trans-2-nonenal is replaced by trans-2- nonenol, or the acetal orester derivatives employed herein or cis-2-nonenol, there is obtained asimilar flavor improvement.

EXAMPLE XIX Two hundred pounds of whole roasted coffee are introducedinto a commercial oil expeller and expressed. Sixteen pounds of oil areobtained, which are clarified by filtration. Twelve pounds of clarifiedoil and 4 pounds of fines are obtained. The clarified oil is stored at50F under carbon dioxide until ready for use.

The expeller cake resulting from the expression of the coffee ispelletized. The pellets are added to 800 pounds of roasted and groundcoffee. The mixture is introduced into a conventional commercial coffeeextractor and is extracted with 3,000 pounds of water under conventionalcoffee percolation techniques used in soluble coffee production. Threehundred pounds of soluble solids are extracted and collected as a liquidextract weighing 900 pounds. The extract is cooled to 60F and 720 poundsof the extract are then spray dried by conventional coffee spray dryingto obtain a soluble coffee powder having 3% moisture. The remaining 180pounds of the extract are divided into two 90 pound portions. Six poundsof the expressed oil are warmed to 65F and dispersed in 90 pounds ofextract by homogenization at 2,000 psig. Fifty milligrams of trans-2-nonenal, dispersed in a liter of water, are added to the other 90 poundsof extract and mixed. The two 90 pound batches are then combined andfrozen at a thickness of Va inch in trays in a period of about one hourto a temperature of 30F. The frozen mixture of extract and aromas isthen freeze dried in a commercial freeze drying unit. The freezeconcentrate is then combined with the spray dried powder.

Instead of freeze drying the aroma concentrate, it may be spray driedand then blended in a similar manner.

Instead of employing freeze dried coffee as the carrier for thetrans-Z-nonenal, the flavor may be incorporated in a film formingsubstance, dried and ground to a fine powder. The powdered concentratemay then be dry blended with the spray dried soluble coffee prepared asabove.

Example XIX may be modified to produce a soluble coffee havingtrans-2-nonenal incorporated throughout all of the soluble powder. Theentire 900 pounds of extract are collected and 40 milligrams of trans-2-nonenal in 2 liters of aqueous 5% ethanolic solution added thereto andblended by mixing until a homogeneous mixture is obtained. Theextract-trans-Z-nonenal mixture is then spray dried or freeze dried toproduce a flavor enhanced soluble coffee.

When the above processes are repeated employing trans-Z-nonenol fortrans-2-nonenal, there is obtained aromatized coffee products.

EXAMPLE XX Trans-2-nonenal (5 mg in one ml ofethanol) is added to 500 mlof distilled water and the aqueous mixture poured into 52 pounds ofcoffee extract of 28.2% coffee solids. The coffee-nonenal mixture isstirred and then poured into trays and frozen to form inch thick slabs.Control slabs are also prepared from the same extract without theaddition of flavors.

The slabs are freeze dried in a 50 square foot Stokes Freeze Drier undermicrons pressure. The freeze drier shelf temperature is lowered from 22Cto 8C during the first 15 minutes of drying, then raised progressivelyto 50C during the next 45 minutes of drying and then progressivelylowered to 30C over the next twenty-two hours of drying. Condensertemperature is maintained at 40F.

The dry product is removed from the drier, broken up and stored.

A flavor evaluation is made by dissolving 0.65 gms of trans-2-nonenalaromatized freeze dried coffee and 2.60 gms of freeze dried control ineight ounces of hot water to give a theoretical 2 ppb concentration.Control cups are prepared by dissolving 3.25 gms of freeze dried controlcoffee in eight ounces of hot water and adding thereto 10 microliters ofa 5 ml aqueous solution containing 0.25 mg trans-2-nonenal to give a 2ppb concentration.

The freeze dried aromatized sample was judged to contain about ninetypercent of the woody flavor of the control, indicating a slight loss oftrans-Z-nonenal aroma during freeze drying.

Trans-2-nonenal is replaced by trans-2-nonenol and the above procedurerepeated to produce aromatized freeze dried coffee.

EXAMPLE XXI To 500 ml of distilled water is added 2.34 mg oftrans-Z-nonenal dissolved in 1 ml of ethanol. The aqueous mix is addedto 40 pounds of coffee extract (24.5% solids) and the mixture is spraydried.

Unaromatized extract is spray dried under equivalent conditions for useas a control. A flavor evaluation is made by dissolving 3.25 g of thearomatized coffee in eight ounces of hot water. Control cups areprepared by dissolving in each cup 3.25 g of control coffee in eightounces of hot water and then adding thereto 10 microliters of a solutionof 0.24 mg trans-2-nonenal in 5 ml of water.

A triangular, odd cup flavor evaluation found no difference between thecups, indicating no significant loss of trans-2-nonenal during spraydrying.

EXAMPLE XXII To 25 grams of Wesson oil is added 1.75 milligrams oftrans-2-nonenal. The resulting mixture is added to a solution of 500grams of gum arabic dissolved in 1 liter of water. The mixture isemulsified and spray dried to give a concentrate.

The concentrate is blended at a 5% by weight level with foodstuffs suchas spray dried and freeze dried soluble coffee to enhance the regularcoffee flavor of beverages produced from these soluble coffees.

When trans-2-nonenal is replaced with trans-2- nonenol a concentrate isobtained, which when added to coffee gives enhanced coffee flavor.

EXAMPLE XXIII EXAMPLE XXIV A flavor comparison similar to Example XI ismade using 100 percent Robusta spray dried soluble coffee having addedthereto 2 ppb of trans-2-nonenal. Compared to control, the flavorenhanced brew had an im- 5 proved woody cup flavor and aroma.

When trans-2-nonenal is replaced by 2 ppb of trans- 2-nonenol, there isobtained a similar woody flavor and aroma.

EXAMPLE xxv To various foodstuffs is added minute amounts of theenhancing compounds of this invention at the proportions indicated. Thefoodstuffs are then evaluated by comparison to a control not containingthe enhancer.

Results are reported in the following table.

TYPICAL EVALUATION OF Z-NONENE-l-AL AND Z-NONENE-l-OL IN VARIOUSPRODUCTS Example Concentration of Trans-2-nonene-l-al Number Product0.12 ppb 0.25 ppb 0.5 ppb 1 ppb 2 ppb 4 ppb I Cola beverage Enhancedcola flavor Woody More like Coke" 1 Nice, woody flavor 2 Pear nectarIncreased pear flavor 3 Ginger ale Enhanced ginger ale Woody flavorSlight woody flavor 4 Black cherry Slight woody Smoother flavor gelatindessert character Woody 5 Cranberry juice Slightly Less astringent Woodyless Woody astringent 6 Vanilla instant More vanilla pudding Morenatural Nice woody 7 Condensed Fuller Meatier More vegetable High Woodybeef broth flavor, and character meatier, smoother More roasted smoothercharacter Smoother flavor 8 Root Beer Enhanced flavor High woodybeverage 9 Creme Soda More creme High woody character Woody 10 Maple andMore maple sugar syrup More buttery Woody character 1 1 Cherry gelatinBetter flavor balance,- More natural than control Woody dessert smootherflavor Eliminates cheap candy cherry character Smoother Definiteimprovement 1 la Artificially More Smoother sweetened flavor bettercherry gelatin balanced flavor l2 Artificially Higher cola flavor Woodysweetened cola Smoother flavor beverage Higher apparent carbonation 13Meat broth Higher flavor impact More meaty but unbalanced ExampleConcentration of Trans-Z-nonene-l-ol Number Product 1.2 ppb 2.5 ppb 5.0ppb l0 ppb ppb ppb l4 Cranberry juice Less Reduced astringency Less Lessastringent astringent, acid impact Definite Woody enhanced improvementflavor 15 Maple and More maple sugar syrup Covers undesirable harshcharacter of product Smoother 16 Meat Broth I'Iigher flavor Beefiermtenslty meatler but fatty 17 Artificially m th sweetened balancedcherry gelatin flavor EFFECT OF COMBINATION OF 2-NONENE-l-AL ANDZ-NONENE-l-OL Continued Example Product Control Evaluation l8 SS PierceCranberry Juice Tart, 0.13 ppb Nonene-l-al Astringent Cranberry 1.3 ppbNonene-l-ol Less stringent 0.25 ppb Nonene-l-al 2.5 ppb Nonene-l-ol Lessstringent More Cranberry While the characteristic woody flavor of theenhancers are acceptable in some of the foodstuffs tested, the enhancersmay be added at below the flavor threshold concentration. For example,the concentration of 2- nonene-l-ol added to cranberry juice should beabout ppb and not ppb where the woody character of the enhancer becomesprominent. 1

EXAMPLE XXVI A solution of trans-2-nonenal was prepared by dissolving 20mg of the aldehyde in 50 ml of ethanol. One half of a milliliter of theresulting solution was then dissolved in 50 ml of spring water to yielda 0.2 mg/SO ml solution. The spring water solution was employed toprepare enhanced instant Postum by adding a sufficient amount to twograms of Postum dissolved in 200 ml of boiling spring water to give 5,10, 20, and ppb concentrations of nonenal in the hot Postum beverage.These beverages were compared with a control of 2 grams Postum dissolvedin 200 ml boiling spring water by several expert tasters. The samplescontaining 5 ppb and 10 ppb nonenal were preferred. The nonenal reducedappreciably the characteristic molasses flavor of Postum and imparted aslight woody flavor. There was a significant reduction in the sweet,cereal taste of the beverage. When trans- 2-nonenol is employed, similarresults are obtained.

Obviously, many modifications and variations of the present inventionare possible in light of the above teachings. It is therefore understoodthat, within the scope of the appended claims, the invention may bepracticed otherwise than as specifically described.

What is claimed is:

l. A process for enhancing the flavor of a non-coffee based foodstuffscomprising adding thereto a compound selected from the group consistingof 2-nonenal, 2-nonenol, lower alkyl acetals of 2-nonenal, esters oforganic acids and 2-nonenol in which the carbonyl is not conjugated witha double bond or aromatic ring, and mixtures thereof, said compoundbeing added in an amount sufficient to enhance the flavor of thefoodstuff without imparting a fatty flavor.

2. The process of claim 1 in which the foodstuff is a beverage.

3. The process of claim 2 in which the beverage is fruit or rootflavored.

4. The process of claim 3 in which the beverage is a dry mix.

5. The process of claim 3 in which the beverage is artificiallysweetened.

6. The process of claim 3 in which the beverage is selected from thegroup consisting of cola, root beer, and gingerale.

7. The process of claim 3 in which the beverage contains cranberryjuice.

8. The process of claim 2 in which the beverage is cereal based.

9. The process of claim 8 in which the beverage also is molasses based.

10. The process of claim 2 in which the beverage is alcohol based.

11. The process of claim 1 in which the foodstuff is a gel.

12. The process of claim 11 in which the gel is gelatin based.

13. The process of claim 11 in which the gel is pectin based.

14. The process of claim 11 in which the gel is cranberry.

15. The process of claim I in which the foodstuff is meat.

16. The process of claim 15 in which the meat is a meat broth.

17. The process of claim 1 in which the foodstuff is sugar based.

18. The process of claim 17 in which the foodstuff contains maple sugar.

19. The process of claim 17 in which the foodstuff is a fruit flavoredcandy.

3,886,297 May 27, 1975 Patent No. Dated lnventofls) Thomas H. Parliment,et al.

It is certified that error appears in the above-identified patent andthat said Letters Patent are hereby corrected as shown below:

In Column 3, line 16, after "flavor" delete -of foodstuffs-.

In Column 3, line 51, change CH (CH CH CH c to H CH (CH CH CH Cthirtieth Day of September 1975 [SEAL] Arrest:

RUTH C. MASON C. MARSHALL DANN Alu'sling Officer Commissioner of Purenrsand Trademarks

1. A PROCESS FOR ENHANCING THE FLAVOR OF A NON-COFFEE BASED FOODSTUFFSCOMPRISING ADDING THERETO A COMPOUND SELECTED FROM THE GROUP CONSISTINGOF 2-NONENAL, 2-NONENOL, LOWER ALKYL ACETALS OF 2-NONENAL, ESTERS OFORGANIC ACIDS AND 2-NONENOL IN WHICH THE CARBONYL IS NOT CONJUGATED WITHA DOUBLE BOND OR AROMATIC RING, AND MIXTURES THEREOF, SAID COMPOUNDBEING ADDED IN AN AMOUNT SUFFICIENT TO ENHANCE THE FLAVOR OF THEFOODSTUFF WITHOUT IMPARTING A FATTY FLAVOR.
 2. The process of claim 1 inwhich the foodstuff is a beverage.
 3. The process of claim 2 in whichthe beverage is fruit or root flavored.
 4. The process of claim 3 inwhich the beverage is a dry mix.
 5. The process of claim 3 in which thebeverage is artificially sweetened.
 6. The process of claim 3 in whichthe beverage is selected from the group consisting of cola, root beer,and gingerale.
 7. The process of claim 3 in which the beverage containscranberry juice.
 8. The process of claim 2 in which the beverage iscereal based.
 9. The process of claim 8 in which the beverage also ismolasses based.
 10. The process of claim 2 in which the beverage isalcohol based.
 11. The process of claim 1 in which the foodstuff is agel.
 12. The process of claim 11 in which the gel is gelatin based. 13.The process of claim 11 in which the gel is pectin based.
 14. Theprocess of claim 11 in which the gel is cranberry.
 15. The process ofclaim 1 in which the foodstuff is meat.
 16. The process Of claim 15 inwhich the meat is a meat broth.
 17. The process of claim 1 in which thefoodstuff is sugar based.
 18. The process of claim 17 in which thefoodstuff contains maple sugar.
 19. The process of claim 17 in which thefoodstuff is a fruit flavored candy.